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WO2021045460A1 - Composé hétérocyclique et dispositif électroluminescent organique le comprenant - Google Patents

Composé hétérocyclique et dispositif électroluminescent organique le comprenant Download PDF

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Publication number
WO2021045460A1
WO2021045460A1 PCT/KR2020/011620 KR2020011620W WO2021045460A1 WO 2021045460 A1 WO2021045460 A1 WO 2021045460A1 KR 2020011620 W KR2020011620 W KR 2020011620W WO 2021045460 A1 WO2021045460 A1 WO 2021045460A1
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substituted
unsubstituted
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heterocyclic
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Korean (ko)
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이영진
박성종
정원장
김동준
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LT Materials Co Ltd
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LT Materials Co Ltd
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Priority to US17/600,149 priority Critical patent/US20220223795A1/en
Priority to CN202080034078.9A priority patent/CN113840822A/zh
Publication of WO2021045460A1 publication Critical patent/WO2021045460A1/fr
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Definitions

  • the present specification relates to a heterocyclic compound and an organic light emitting device including the same.
  • An electroluminescent device is a type of self-luminous display device, and has advantages in that it has a wide viewing angle, excellent contrast, and a fast response speed.
  • the organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes are combined in the organic thin film to form a pair, and then emit light while disappearing.
  • the organic thin film may be composed of a single layer or multiple layers as necessary.
  • the material of the organic thin film may have a light emitting function as needed.
  • a compound capable of constituting an emission layer by itself may be used, or a compound capable of serving as a host or a dopant of the host-dopant-based emission layer may be used.
  • a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection may be used.
  • the present specification is to provide a heterocyclic compound and an organic light-emitting device including the same.
  • a heterocyclic compound represented by the following Formula 1 is provided.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 divalent heterocyclic group,
  • R104, R105, R104' and R105' are each independently hydrogen; heavy hydrogen; Halogen group; Alkyl group; Alkenyl group; Alkoxy group; Cycloalkyl group; Aryl group; Or a heterocyclic group,
  • r1 and r2 are each an integer of 1 to 3,
  • r3 is an integer from 1 to 4,
  • l1 to l3 and z'1 to z'3 are each independently an integer of 1 to 5,
  • the first electrode A second electrode provided to face the first electrode; And an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes at least one heterocyclic compound represented by Formula 1 above.
  • the compound described herein can be used as a material for an organic material layer of an organic light-emitting device.
  • the compound may serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like in an organic light emitting device.
  • the compound may be used as a material for an electron transport layer, a hole blocking layer, and a charge generation layer of an organic light-emitting device.
  • Formula 1 has a structure in which terpyridine is di- or tri-substituted, thereby increasing the stability of the molecule by increasing the delocalization of electrons compared to the mono-substituted compound, which affects the stability of the device and improves the device performance. .
  • the driving voltage of the device may be lowered, light efficiency may be improved, and the lifespan characteristics of the device may be improved.
  • 1 to 5 are diagrams each exemplarily showing a stacked structure of an organic light-emitting device according to an exemplary embodiment of the present specification.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to a C1 to C60 linear or branched alkyl group; C2 to C60 linear or branched alkenyl group; C2 to C60 linear or branched alkynyl group; C1 to C60 alkoxy group; C3 to C60 monocyclic or polycyclic cycloalkyl group; C2 to C60 monocyclic or polycyclic heterocycloalkyl group; C6 to C60 monocyclic or polycyclic aryl group; C2 to C60 monocyclic or polycyclic heterocyclic group; Silyl group; Phosphine oxide group; And substituted or unsubstituted with one or more substituents selected from the group consisting of an amine group, or substituted or unsubstituted with a substituent to which two or more substituents selected from the above exemplified substituents are connected.
  • "when a substituent is not indicated in the chemical formula or compound structure” may mean that all positions that can come as a substituent are hydrogen or deuterium. That is, deuterium is an isotope of hydrogen, and some hydrogen atoms may be deuterium, which is an isotope, and in this case, the content of deuterium may be 0% to 100%.
  • the content of deuterium is 0%, the content of hydrogen is 100%, and all of the substituents explicitly exclude deuterium such as hydrogen. If not, hydrogen and deuterium may be mixed and used in the compound.
  • deuterium is one of the isotopes of hydrogen and is an element having a deuteron consisting of one proton and one neutron as a nucleus, and hydrogen- It can be represented by 2, and elemental symbols may be written as D or H 2.
  • an isotope meaning an atom having the same atomic number (Z) but different mass number (A) has the same number of protons, but neutrons
  • the number of (neutron) can be interpreted as other elements.
  • the total number of substituents that the phenyl group can have is 5 (T1 in the formula), of which the number of deuterium is 1 (T2 in the formula), it will be expressed as 20%.
  • T1 in the formula the total number of substituents that the phenyl group can have
  • T2 in the formula the number of deuterium is 1
  • I can. That is, it can be represented by the following structural formula that the content of deuterium in the phenyl group is 20%.
  • the "phenyl group having a deuterium content of 0%” may mean a phenyl group that does not contain deuterium atoms, that is, has 5 hydrogen atoms.
  • the halogen may be fluorine, chlorine, bromine or iodine.
  • the alkyl group includes a straight chain or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents.
  • the number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, more specifically, 1 to 20.
  • Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group,
  • the alkenyl group includes a linear or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically, 2 to 20.
  • Specific examples include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(Naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • the alkynyl group includes a linear or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically, 2 to 20.
  • the alkoxy group may be a straight chain, branched chain, or cyclic chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is 1 to 60 carbon atoms, and preferably 1 to 30 carbon atoms.
  • the cycloalkyl group includes monocyclic or polycyclic having 3 to 60 carbon atoms, and may be further substituted by other substituents.
  • the polycyclic refers to a group in which a cycloalkyl group is directly connected or condensed with another ring group.
  • the other cyclic group may be a cycloalkyl group, but may be a different type of cyclic group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, and the like.
  • the number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20.
  • the heterocycloalkyl group includes O, S, Se, N or Si as a hetero atom, includes monocyclic or polycyclic having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the polycyclic means a group in which a heterocycloalkyl group is directly connected or condensed with another ring group.
  • the other cyclic group may be a heterocycloalkyl group, but may be a different type of cyclic group, such as a cycloalkyl group, an aryl group, a heterocyclic group, and the like.
  • the number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.
  • the aryl group includes monocyclic or polycyclic having 6 to 60 carbon atoms, and may be further substituted by other substituents.
  • the polycyclic refers to a group in which an aryl group is directly connected or condensed with another ring group.
  • the other cyclic group may be an aryl group, but may be another type of cyclic group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, and the like.
  • the aryl group includes a spiro group.
  • the number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25.
  • aryl group examples include phenyl group, biphenyl group, triphenyl group, naphthyl group, anthryl group, chrysenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenalenyl group, pyre Nyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, condensed ring groups thereof And the like, but are not limited thereto.
  • the silyl group is a substituent including Si and the Si atom is directly connected as a radical, and is represented by -Si(R101)(R102)(R103), and R101 to R103 are the same as or different from each other, and each independently Hydrogen; heavy hydrogen; Halogen group; Alkyl group; Alkenyl group; Alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heterocyclic group.
  • silyl group examples include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. It is not limited.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • the heterocyclic group includes O, S, SO, SO 2 , Se, N or Si as a hetero atom, and includes a monocyclic or polycyclic having 2 to 60 carbon atoms, and to be further substituted by other substituents.
  • the polycyclic means a group in which a heterocyclic group is directly connected or condensed with another ring group.
  • the other cyclic group may be a heterocyclic group, but may be a different type of cyclic group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, and the like.
  • the number of carbon atoms of the heterocyclic group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25.
  • heterocyclic group examples include pyridyl group, pyrrolyl group, pyrimidyl group, pyridazinyl group, furanyl group, thiophene group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl Group, isothiazolyl group, triazolyl group, furazinyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , Thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozoliryl group, naphthyridyl group,
  • the phosphine oxide group may be substituted with an aryl group, and the above-described example may be applied to the aryl group.
  • the phosphine oxide group includes a diphenylphosphine oxide group, a dinaphthylphosphine oxide, and the like, but is not limited thereto.
  • the amine group is represented by -N(R106)(R107), R106 and R107 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Alkyl group; Alkenyl group; Alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heterocyclic group.
  • the amine group is a monoalkylamine group; Monoarylamine group; Monoheteroarylamine group; -NH 2 ; Dialkylamine group; Diarylamine group; Diheteroarylamine group; Alkylarylamine group; Alkylheteroarylamine group; And it may be selected from the group consisting of an arylheteroarylamine group, the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine group examples include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, dibiphenylamine group, anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluore
  • nilamine group phenyltriphenylenylamine group, biphenyltriphenylenylamine group, and the like, but are not limited thereto.
  • the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted.
  • I can.
  • two substituents substituted with an ortho position in a benzene ring and two substituents substituted with the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.
  • a heterocyclic compound represented by Formula 1 is provided.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 divalent heterocyclic group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted C6 to C40 arylene group; Or a substituted or unsubstituted C2 to C40 divalent heterocyclic group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted C6 to C20 arylene group; Or a substituted or unsubstituted C2 to C20 divalent heterocyclic group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted C6 to C20 arylene group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a biphenylene group.
  • L1 is a direct bond; Phenylene group; Or a biphenylene group.
  • L2 and L3 are the same as or different from each other, and each independently a direct bond; Or a phenylene group.
  • R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heterocyclic group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C3 to C60 aliphatic hydrocarbon ring, a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring, Or to form a substituted or unsubstituted C2 to C60 heterocycle.
  • R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C40 alkyl group; A substituted or unsubstituted C6 to C40 aryl group; Or a substituted or unsubstituted C2 to C40 heterocyclic group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C3 to C40 aliphatic hydrocarbon ring, a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring, Or to form a substituted or unsubstituted C2 to C40 heterocycle.
  • R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heterocyclic group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C3 to C20 aliphatic hydrocarbon ring, a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring, Or to form a substituted or unsubstituted C2 to C20 heterocycle.
  • R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heterocyclic group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.
  • R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heterocyclic group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted benzene ring.
  • R1 is hydrogen; Or deuterium.
  • R1 is hydrogen
  • R2 and R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C6 to C20 aryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.
  • r2 is 1, R2 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C60 aryl group.
  • r2 is 1, R2 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C40 aryl group.
  • r2 is 1, R2 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C20 aryl group.
  • r2 is 1, R2 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted phenyl group.
  • r2 is 1, R2 is hydrogen; heavy hydrogen; Or a phenyl group.
  • r2 is 2, and a plurality of R2 are bonded to each other to form a substituted or unsubstituted C3 to C20 aliphatic hydrocarbon ring, a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring, or a substituted or It forms an unsubstituted C2 to C20 heterocycle.
  • r2 is 2, and a plurality of R2 are bonded to each other to form a substituted or unsubstituted C3 to C20 aliphatic hydrocarbon ring, or a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring. .
  • r2 is 2, and a plurality of R2s combine with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.
  • r2 is 2, and a plurality of R2s combine with each other to form a C6 to C20 aromatic hydrocarbon ring.
  • r2 is 2, and a plurality of R2s combine with each other to form a benzene ring.
  • r3 is 1, R3 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C60 aryl group.
  • r3 is 1, R3 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C40 aryl group.
  • r3 is 1, R3 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C20 aryl group.
  • r3 is 1, R3 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted phenyl group.
  • r3 is 1, R3 is hydrogen; heavy hydrogen; Or a phenyl group.
  • r3 is 2, and a plurality of R3 are bonded to each other to form a substituted or unsubstituted C3 to C20 aliphatic hydrocarbon ring, a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring, or a substituted or It forms an unsubstituted C2 to C20 heterocycle.
  • r3 is 2, and a plurality of R3s combine with each other to form a substituted or unsubstituted C3 to C20 aliphatic hydrocarbon ring or a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.
  • r3 is 2, and a plurality of R3s combine with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.
  • r3 is 2, and a plurality of R3s are bonded to each other to form a C6 to C20 aromatic hydrocarbon ring.
  • r3 is 2, and a plurality of R3s are bonded to each other to form a benzene ring.
  • Formula 1 may be represented by any one of Formulas 1-1 to 1-4 below.
  • L11 to L13 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group,
  • R104, R105, R104' and R105' are each independently hydrogen; heavy hydrogen; Halogen group; Alkyl group; Alkenyl group; Alkoxy group; Cycloalkyl group; Aryl group; Or a heterocyclic group.
  • L11 to L13 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted C6 to C40 arylene group.
  • L11 to L13 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted C6 to C20 arylene group.
  • L11 to L13 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
  • L11 to L13 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a biphenylene group.
  • L11 is a direct bond; Phenylene group; Or a biphenylene group.
  • L12 and L13 are the same as or different from each other, and each independently a direct bond; Or a phenylene group.
  • Z12 and Z13 are the same as or different from each other, and each independently a halogen group; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; Or a substituted or unsubstituted carbazole group.
  • Z12 and Z13 are the same as or different from each other, and each independently a halogen group; Cyano group; Methyl group; A pyrimidine group unsubstituted or substituted with an aryl group; A triazine group unsubstituted or substituted with an aryl group; Or a carbazole group unsubstituted or substituted with an aryl group.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heterocyclic group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C40 alkyl group; A substituted or unsubstituted C6 to C40 aryl group; Or a substituted or unsubstituted C2 to C40 heterocyclic group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heterocyclic group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.
  • R11 is hydrogen; Or deuterium.
  • R11 is hydrogen
  • R12 and R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; Or a substituted or unsubstituted C6 to C20 aryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.
  • r2 is 1, R12 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C60 aryl group.
  • r2 is 1, R12 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C40 aryl group.
  • r2 is 1, R12 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C20 aryl group.
  • r2 is 1, R12 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted phenyl group.
  • r2 is 1, R12 is hydrogen; heavy hydrogen; Or a phenyl group.
  • r2 is 2, and a plurality of R12 are bonded to each other to form a substituted or unsubstituted C3 to C20 aliphatic hydrocarbon ring, a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring, or a substituted or It forms an unsubstituted C2 to C20 heterocycle.
  • r2 is 2, and a plurality of R12 are bonded to each other to form a substituted or unsubstituted C3 to C20 aliphatic hydrocarbon ring, or a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring. .
  • r2 is 2, and a plurality of R12 are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.
  • r2 is 2, and a plurality of R12 are bonded to each other to form a C6 to C20 aromatic hydrocarbon ring.
  • r2 is 2, and a plurality of R12 are bonded to each other to form a benzene ring.
  • r3 is 1, R13 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C60 aryl group.
  • r3 is 1, R13 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C40 aryl group.
  • r3 is 1, R13 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C20 aryl group.
  • r3 is 1, R13 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted phenyl group.
  • r3 is 1, R13 is hydrogen; heavy hydrogen; Or a phenyl group.
  • r3 is 2, and a plurality of R13 are bonded to each other to form a substituted or unsubstituted C3 to C20 aliphatic hydrocarbon ring, a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring, or a substituted or It forms an unsubstituted C2 to C20 heterocycle.
  • r3 is 2, and a plurality of R13 are bonded to each other to form a substituted or unsubstituted C3 to C20 aliphatic hydrocarbon ring, or a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.
  • r3 is 2, and a plurality of R13 is bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.
  • r3 is 2, and a plurality of R13 is bonded to each other to form a C6 to C20 aromatic hydrocarbon ring.
  • r3 is 2, and a plurality of R13 are bonded to each other to form a benzene ring.
  • Formula 1 may be represented by any one of the following compounds, but is not limited thereto.
  • a compound having the inherent characteristics of the introduced substituent can be synthesized.
  • a hole injection layer material, a hole transport layer material, a light emitting layer material, an electron transport layer material, and a substituent mainly used in the charge generation layer material used in manufacturing an organic light emitting device are introduced into the core structure to meet the conditions required by each organic material layer. Materials can be synthesized.
  • the energy band gap can be finely adjusted, while the properties at the interface between organic substances can be improved, and the use of the material can be varied.
  • the first electrode A second electrode; And an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes at least one heterocyclic compound represented by Formula 1 above.
  • the first electrode may be an anode
  • the second electrode may be a cathode
  • the first electrode may be a cathode
  • the second electrode may be an anode
  • the organic light-emitting device may be a blue organic light-emitting device
  • the heterocyclic compound according to Formula 1 may be used as a material of the blue organic light-emitting device.
  • the heterocyclic compound according to Formula 1 may be included in an electron transport layer, a hole blocking layer, or a charge generation layer of a blue organic light-emitting device.
  • the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound according to Formula 1 may be used as a material of the green organic light-emitting device.
  • the heterocyclic compound according to Formula 1 may be included in an electron transport layer, a hole blocking layer, or a charge generation layer of a green organic light-emitting device.
  • the organic light-emitting device may be a red organic light-emitting device
  • the heterocyclic compound according to Formula 1 may be used as a material of the red organic light-emitting device.
  • the heterocyclic compound according to Formula 1 may be included in an electron transport layer, a hole blocking layer, or a charge generation layer of a red organic light-emitting device.
  • the organic light-emitting device of the present specification may be manufactured by a conventional method and material of an organic light-emitting device, except for forming one or more organic material layers using the above-described heterocyclic compound.
  • the heterocyclic compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic material layers.
  • the organic material layer may include an electron transport layer, and the electron transport layer may include the heterocyclic compound of Formula 1 above.
  • the organic material layer may include a hole blocking layer, and the hole blocking layer may include the heterocyclic compound of Formula 1 above.
  • the organic light emitting device of the present invention may further include one layer or two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.
  • FIG. 1 to 5 illustrate a stacking sequence of an electrode and an organic material layer of an organic light-emitting device according to an exemplary embodiment of the present specification.
  • the scope of the present application be limited by these drawings, and the structure of an organic light-emitting device known in the art may be applied to the present application.
  • an organic light-emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is shown.
  • an organic light-emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.
  • the organic light emitting device according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, an electron transport layer 305, and an electron injection layer 306, and the organic light emitting device according to FIG. 4 It includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306.
  • the scope of the present application is not limited by such a lamination structure, and other layers other than the light emitting layer may be omitted, or other necessary functional layers may be further added if necessary.
  • the organic material layer including the heterocyclic compound represented by Formula 1 may further include other materials as necessary.
  • the organic light-emitting device includes an anode, a cathode, and two or more stacks provided between the anode and the cathode, and the two or more stacks each independently include an emission layer, and the two or more stacks
  • a charge generation layer is included between the liver, and the charge generation layer includes a heterocyclic compound represented by Formula 1 above.
  • the organic light-emitting device includes an anode, a first stack provided on the anode and including a first emission layer, a charge generation layer provided on the first stack, and a charge generation layer. And a second stack provided on and including a second emission layer, and a cathode provided on the second stack.
  • the charge generation layer may include a heterocyclic compound represented by Formula 1 above.
  • An organic light-emitting device includes: a first electrode; A first stack provided on the first electrode and including a first emission layer; A charge generation layer provided on the first stack; A second stack provided on the charge generation layer and including a second emission layer; And a second electrode provided on the second stack, and the charge generation layer may include a heterocyclic compound represented by Formula 1 above.
  • An organic light-emitting device includes: a first electrode; A second electrode; And an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes two or more stacks, each of the two or more stacks independently includes a light emitting layer, and charge between the two or more stacks A generation layer is included, and the charge generation layer may include a heterocyclic compound represented by Formula 1 above.
  • An organic light-emitting device includes: a first electrode; A second electrode; And a first stack including an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes a first emission layer; A charge generation layer provided on the first stack; And a second stack including a second emission layer provided on the charge generation layer, wherein the charge generation layer may include a heterocyclic compound represented by Formula 1 above.
  • the charge generation layer includes an N-type charge generation layer, and the N-type charge generation layer includes a heterocyclic compound represented by Formula 1 above.
  • the charge generation layer may further include a P-type charge generation layer.
  • an organic light-emitting device having a two-stack tandem structure is exemplarily shown in FIG. 5 below.
  • the first electron blocking layer, the first hole blocking layer, and the second hole blocking layer described in FIG. 5 may be omitted in some cases.
  • the cathode material Materials having a relatively large work function may be used as the cathode material, and transparent conductive oxides, metals, or conductive polymers may be used.
  • the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material Materials having a relatively low work function may be used as the cathode material, and metal, metal oxide, or conductive polymer may be used.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • a known hole injection material may be used.
  • a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a phthalocyanine compound disclosed in [Advanced Material, 6, p.677 (1994)] is described.
  • Starburst type amine derivatives such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine (m- MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline/dodecylbenzenesulfonic acid or poly( 3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), polyaniline/camphor sulfonic acid or polyaniline/ Poly(4-styrenesulfonate) (Polyaniline/Poly(4-styrenesulfonate)) or the like may be used.
  • TCTA tris(
  • hole transport material pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like may be used, and low molecular weight or high molecular weight materials may be used.
  • Electron transport materials include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, fluorenone Derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like may be used, and not only low-molecular substances but also high-molecular substances may be used.
  • LiF is typically used in the art, but the present application is not limited thereto.
  • Red, green, or blue light-emitting materials may be used as the light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. In this case, two or more light-emitting materials may be deposited as separate sources and used, or premixed and deposited as one source. Further, a fluorescent material may be used as the light emitting material, but it may also be used as a phosphorescent material. As the light emitting material, a material that emits light by combining holes and electrons respectively injected from the anode and the cathode may be used, but materials in which a host material and a dopant material are both involved in light emission may be used.
  • hosts of the same series may be mixed and used, or hosts of different types may be mixed and used.
  • any two or more types of an n-type host material or a p-type host material may be selected and used as the host material of the light emitting layer.
  • the organic light-emitting device may be a top emission type, a bottom emission type, or a double-side emission type depending on the material used.
  • the heterocyclic compound according to an exemplary embodiment of the present specification may act on a principle similar to that applied to an organic light-emitting device in organic electronic devices, including organic solar cells, organic photoreceptors, and organic transistors.
  • the target compound of Table 1 was synthesized in the same manner as in Preparation of Compound 1, except that compounds A, B, C, and D of Table 1 were used instead of A, B, C, and D of Preparation Example 1.
  • the target compound of Table 2 was synthesized in the same manner as in Preparation of Compound 167, except that compounds A, B, C, and D of Table 2 were used instead of A, B, C, and D of Preparation Example 2.
  • the transparent electrode ITO thin film obtained from OLED glass was subjected to ultrasonic cleaning for 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water in sequence, and then stored in isopropanol and used.
  • the ITO substrate is installed in the substrate folder of the vacuum evaporation equipment, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine ( 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was added.
  • NPB N,N'-bis( ⁇ -naphthyl)-N,N'-diphenyl-4,4'-diamine
  • a blue light emitting material having the following structure was deposited as a light emitting layer thereon. Specifically, H1, a blue light-emitting host material, was vacuum-deposited to a thickness of 200 ⁇ in one cell in the vacuum deposition equipment, and D1, a blue light-emitting dopant material, was vacuum-deposited 5% compared to the host material.
  • lithium fluoride LiF
  • Al anode As an electron injection layer, lithium fluoride (LiF) was deposited to a thickness of 10 ⁇ , and an OLED device was fabricated using an Al anode to a thickness of 1,000 ⁇ .
  • the organic light-emitting device using the electron transport layer material of the blue organic light-emitting device of the present invention has a lower driving voltage and significantly improved luminous efficiency and lifetime compared to Comparative Examples 1-1 to 1-5. Became.
  • compounds 1, 144, 156, 159, and 161 are excellent in all aspects of driving voltage, efficiency, and life.
  • Example 1-1 has a more planar structure than Comparative Example 1-2 because the HN hydrogen bond of the phenyl linking group located between the azine and terpyridine substituents acts strongly to prevent the rotational motion of the phenyl linking group. Will have.
  • Example 1-1 is composed of a structure in which heteroatoms of terpyridine are unevenly distributed on one side, so that metal binding between lithium and terpyridine substituents occurs strongly between the electron injection layer and the electron transport layer, causing the diffusion of lithium. Can be prevented. Therefore, it is judged that the compound of the present invention has improved electron-transporting characteristics or stability, resulting in excellence in all aspects of driving, efficiency, and life.
  • the transparent electrode ITO thin film obtained from OLED glass was subjected to ultrasonic cleaning for 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water in sequence, and then stored in isopropanol and used.
  • the ITO substrate is installed in the substrate folder of the vacuum evaporation equipment, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine ( 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was added.
  • a current was applied to the cell to evaporate 2-TNATA to deposit a hole injection layer having a thickness of 600 ⁇ on the ITO substrate.
  • the following N,N'-bis( ⁇ -naphthyl)-N,N'-diphenyl-4,4'-diamine (N,N'-bis( ⁇ -naphthyl)-N, N'-diphenyl-4,4'-diamine: NPB) was added, and a hole transport layer having a thickness of 300 ⁇ was deposited on the hole injection layer by evaporation by applying a current to the cell.
  • a blue light emitting material having the following structure was deposited as a light emitting layer thereon. Specifically, H1, a blue light-emitting host material, was vacuum-deposited to a thickness of 200 ⁇ in one cell in the vacuum deposition equipment, and D1, a blue light-emitting dopant material, was vacuum-deposited 5% compared to the host material.
  • a hole blocking layer was formed from the compound shown in Table 6 to a thickness of 50 ⁇ , and then E1 as an electron transport layer was formed to a thickness of 250 ⁇ .
  • lithium fluoride LiF
  • Al anode a thickness of 1,000 ⁇ .
  • all organic compounds required for OLED device manufacturing were vacuum-sublimated and purified under 10 -8 to 10 -6 torr for each material and used for OLED manufacturing.
  • Table 6 shows the results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the blue organic light-emitting device manufactured according to the present invention by performing the same procedure as in Experimental Example 1.
  • Example 2-1 One 4.93 8.00 (0.134, 0.102) 43
  • Example 2-2 2 5.28 6.23 (0.134, 0.101) 35
  • Example 2-3 3 5.23 6.82 (0.134, 0.101) 31
  • Example 2-4 13 5.06 6.57 (0.134, 0.103) 34
  • Example 2-5 14 5.45 6.18 (0.134, 0.102) 26
  • Example 2-6 15 5.50 6.79 (0.134, 0.101) 29
  • Example 2-7 26
  • Example 2-8 73 5.04 7.27 (0.134, 0.102) 49
  • Example 2-9 100 5.14 6.33 (0.134, 0.101) 36
  • Example 2-10 137 5.20 6.69 (0.134, 0.103) 41
  • Example 2-11 141 5.06 6.64 (0.134, 0.101) 25
  • Example 2-12 142 5.45 6.95 (0.134, 0.100) 39
  • Example 2-13 143 5.23 7.39 (0.134, 0.103) 41
  • Example 2-14 144 4.95 6.91 (0.134,
  • the organic electroluminescent device using the hole blocking layer material of the blue organic electroluminescent device of the present invention has a lower driving voltage compared to Comparative Examples 2-1 to 2-4, and luminous efficiency and lifetime This has been significantly improved.
  • the glass substrate coated with ITO thin film to a thickness of 1500 ⁇ was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as acetone, methanol, and isopropyl alcohol, dried, and UVO treated for 5 minutes using UV in a UV scrubber. Thereafter, the substrate was transferred to a plasma cleaner (PT), followed by plasma treatment to remove the ITO work function and residual film in a vacuum state, and transferred to a thermal evaporation equipment for organic deposition.
  • PT plasma cleaner
  • An organic material was formed on the ITO transparent electrode (anode) in a two-stack WOLED (White Orgainc Light Emitting Device) structure.
  • TAPC was first thermally vacuum deposited to a thickness of 300 ⁇ to form a hole transport layer. After the hole transport layer was formed, a light emitting layer was thermally vacuum deposited thereon as follows. The light emitting layer was deposited 300 ⁇ by doping 8% of FIrpic on TCz1 as a host with a blue phosphorescent dopant.
  • the electron transport layer was formed of 400 ⁇ using TmPyPB (1,3,5-Tris(3-pyridyl-3-phenyl)benzene), and on it, E1, E2, E3, BBQB, TBQB were used as comparative examples, As an example, a charge generation layer having a thickness of 100 ⁇ was formed by doping 20% of Cs 2 CO 3 to the compounds shown in Table 7 below.
  • MoO 3 was first thermally vacuum deposited to a thickness of 50 ⁇ to form a hole injection layer.
  • the hole transport layer a common layer, was formed by doping 20% MoO 3 on TAPC to form 100 ⁇ , and then formed by depositing 300 ⁇ TAPC.
  • the emission layer was formed by doping 8% of the green phosphorescent topant Ir (ppy) 3 on the host TCz1. After 300 ⁇ deposition, 600 ⁇ was formed using TmPyPB as an electron transport layer.
  • lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 ⁇ to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 ⁇ to form a cathode.
  • Al aluminum
  • Example 3-1 One 5.31 66.67 (0.218, 0.427) 59
  • Example 3-2 2 5.34 66.16 (0.220, 0.431) 55
  • Example 3-3 3 5.31 65.13 (0.220, 0.431) 49
  • Example 3-4 13 5.24 67.07 (0.200, 0.421) 55
  • Example 3-5 14 5.00 65.48 (0.228, 0.436) 51
  • Example 3-6 15 5.15 67.26 (0.243, 0.442)
  • Example 3-7 26 5.19 65.21 (0.221, 0.433)
  • Example 3-8 73 5.32 66.97 (0,208, 0.415) 57
  • Example 3-9 100 5.31 67.07 (0.233, 0.433) 58
  • Example 3-10 137 4.96 67.54 (0.238, 0.438) 73
  • Example 3-11 141 5.10 67.09 (0.225, 0.429) 49
  • Example 3-12 142 5.35 66.35
  • the organic light-emitting device using the charge generation layer material of the two-stack white organic light-emitting device of the present invention has a lower driving voltage and a luminous efficiency compared to Comparative Examples 3-1 to 3-5. Improved. In particular, it was confirmed that compounds 1, 14, 137, and 445 are remarkably excellent in all aspects of driving voltage, efficiency, and life.
  • the compound of the present invention used as an N-type charge generating layer composed of an invented skeleton having an appropriate length, strength and flat properties and an appropriate hetero compound capable of bonding with a metal is used as an alkali metal or alkaline earth metal. It is presumed that a gap state was formed in the N-type charge generation layer by doping, and electrons generated from the P-type charge generation layer were easily injected into the electron transport layer through the gap state generated in the N-type charge generation layer. Is judged. Accordingly, the P-type charge generation layer enables electron injection and electron transfer to the N-type charge generation layer well, and thus, it is believed that the driving voltage of the organic light emitting device is lowered and the efficiency and lifespan are improved.
  • the core structure of the present application has a substituent at two places, a substituent lacking electrons and an aryl or acene substituent are combined, so that the electron-deficient substituent easily receives electrons from the electron injection layer, and the aryl or acene substituent stabilizes the molecule itself. And by transferring the supplied electrons to the emission layer, it is possible to improve device characteristics.

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Abstract

La présente invention concerne un composé hétérocyclique représenté par la formule chimique 1, et un dispositif électroluminescent organique le comprenant.
PCT/KR2020/011620 2019-09-06 2020-08-31 Composé hétérocyclique et dispositif électroluminescent organique le comprenant Ceased WO2021045460A1 (fr)

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KR20240105539A (ko) * 2022-12-27 2024-07-08 솔루스첨단소재 주식회사 유기 화합물 및 이를 이용한 유기 전계 발광 소자

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